N,N'-Dimethylethylenediamine → 5-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646094Notes

Reaction equation

HRID 646094 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.Br[C:40]1[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][CH:20]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 68475095Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylate

Product 1

HCID 687003415-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterYield 95.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-tert-Butylphenyl)indole-2-carboxylic acid ethyl ester (198 mg, 0.60 mmol; see step (a) above), CuI (12 mg, 0.06 mmol), K3PO4 (254 mg, 1.2 mmol), N,N′-dimethyl-1,2-diaminoethane (20 μL, 0.18 mmol) and 1-bromo-4-isopropoxybenzene (258 mg, 1.2 mmol) in toluene (2 mL) was heated at 110° C. for 17 h. The mixture was diluted with EtOAc and washed with NaHCO3 (aq. sat.), HCl (aq. 0.1 M), brine and then dried over Na2SO4. Concentration and purification by chromatography gave the sub-title compound (260 mg, 94%).

Workup

  1. washwashed with NaHCO3 (aq. sat.), HCl (aq. 0.1 M), brine
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration and purification by chromatography

Sources & evidence

ORD record
ord-e2863fda51484e9780a671f7933b8df4
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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